A vocal Trump critic considering his own future presidential aspirations, Cuban cited the administration's failure to pass healthcare legislation that would have repealed and replaced Obamacare and argued Trump has a long way to go on tax reform.

"He doesn't have a foundation for any tax changes — he's going to find out it's also very complicated," Cuban said, arguing that Trump campaigned on being able to make major policy changes with bipartisan support.

"Now he turns around and says, "No, everybody hates me and nobody's helping me,' you know, and he pouts," Cuban said.

But Cuban, who owns the Dallas Mavericks and campaigned for Hillary Clinton in 2016, also argued that if you view Trump's presidency as "political chemotherapy," then he might deserve a higher grade.